


Farther on Up the Road

by Isis_McGee



Series: How Far 'verse [3]
Category: Supernatural
Genre: Anal Sex, Car Sex, Dom Sam, Established Relationship, Felching, Het Anal, Jess is a little subby in this one, Multi, Oral Sex, Plot What Plot/Porn Without Plot, Rimming, Road Head, Sub Dean
Language: English
Status: Completed
Published: 2015-10-12
Updated: 2015-10-12
Packaged: 2018-04-26 01:08:57
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,563
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4984021
Author URL: https://archiveofourown.org/users/Isis_McGee/pseuds/Isis_McGee
Summary: <blockquote class="userstuff">
              <p>Sam wants to get Dean out of his head while on the move to a new case. He's got a particular idea of how to do that, and Jess is most certainly involved.</p>
            </blockquote>





	Farther on Up the Road

**Author's Note:**

  * For [DickBaggins](https://archiveofourown.org/users/DickBaggins/gifts).



The next hunt was 516 miles away from where Sam, Jess, and Dean were at the moment, but all of them were looking forward to being on the road after having spent nearly a month in Corinth, Mississippi. They were also looking forward to getting out of the southern summer heat and farther north where maybe the humidity wouldn’t be so stifling.

“You sure we don’t want to just head north and relax somewhere? Maybe hit Milwaukee, drink our way through it?” Dean sounded hopeful as he said it, a smile meant to goad them into saying yes on his face. Sam gave him a half smile back and laughed a little and Jess rolled her eyes.

“As much as we might want to take some Miller time, there’s a couple guys in jail cells with no remembrance of committing crimes in Missouri that might need our help,” Jess pointed out. “Plus, taking this hunt so soon was your idea.”

Dean shrugged his bag onto his shoulder and tipped his head in acknowledgment of Jess’ point. Sam and Jess followed suit in shouldering their bags and they were out the door.

Dean spun the keys around his finger as Jess headed for the back seat and Sam shoved their stuff into the trunk. Jess was just opening her door when Sam spoke.

“I’ll take the back, Jess. My ankle’s bothering me from that fall a couple weeks ago and I’ll prop it up.”

Jess narrowed her eyes suspiciously‒ Sam hadn’t complained about his injury for the last week‒ but she shrugged and kissed his cheek as she walked around the car to the passenger seat.

Dean turned to her and whatever he was going to say got cut off.

“I know, I won’t touch the radio without your express permission. It was one time,” Jess protested. She turned and shot Sam a look when he snorted, but Sam caught Dean’s eye in the rearview and they shared their amusement. 

As it turned out, Jess had no desire to touch the radio; Dean had warmed up to the softer side of classic rock since Jess had joined them, and allowed her to slip Joni Mitchell’s _Blue_ into the tape selection. He didn’t change it as it came through the speakers, and Jess even caught him tapping his fingers along as they went down the road. It brought a rush of affection for him, just as the sight of Sam half asleep against the window did for him as well.

Jess and Dean didn’t really talk much, even though the music was down, mostly out of consideration for the fact that Sam had fallen asleep. Dean seemed to be in his own world quite a bit and Jess was content to let him be. She too got lost in her own reverie, so much so that she didn’t even notice Sam had woken up until she felt her phone vibrate and saw his name pop up on the screen. She quirked her mouth up in amusement.

‘ _don’t react to this message. Next time we stop, come sit in the back’_

 _‘sick of the back?’_ she typed back, trying to keep from furrowing her brow.

_‘no. we’re gonna get Dean outta his head.’_

Jess couldn’t keep her eyebrows from flying up and she saw Dean glance her way. She tried to school her face into a neutral expression as quickly as possible, but she wasn’t sure he bought it.

Fifteen minutes passed and Sam cleared his throat, catching Dean’s attention.

“Pit stop next time you can?”

“You gotta pee? I can just pull over.”

‘No, I want some gummy worms.”

Dean rolled his eyes, but it was with a smile tugging at his lips.

“And I’d like to use a toilet to pee,” Jess said.

“Yeah, okay. We can take a break next gas station we see. Though it’s a little early in the trip for that, you know. It’s only been like an hour and a half. This damn Joni Mitchell tape’s still playing for crying out loud.”

Jess didn’t deign to respond to it, and Dean obviously hadn’t expected her to, with the way that he left it playing until it began to click at the end of the tape. The ride to the gas station‒the nearest one was merely 15 miles away‒ was filled with the sound of Jess trying to find something that would be just right. She’d finally settled on something when they pulled to a stop in front of a pump.

The three of them took care of their gas station business efficiently, as though they had a system for it, though they’d never actually established one. It wasn’t long until Jess was opening the door to the backseat and crawling in after Sam. Sam set the bag of snacks and pop over the seat to rest where Jess had been.

Dean turned around to look at them with a question in his eyes. Before he could open his mouth to ask anything, Jess had leveled him with a stare.

“Drive, Dean,” she commanded. “And keep your eyes on the road until I tell you otherwise.”

He turned back around, but he caught Jess’ eye in the rearview. She arched a brow commandingly and Dean looked away.

“Yes, ma’am.”

Jess and Sam smiled at each other. The glint in both of their eyes would have frightened Dean if he could see them‒ and gotten him halfway to hard. It didn’t leave either of them totally unaffected either.

They moved to the middle of the backseat and Jess threw a leg over Sam’s lap. His hands immediately went to her hips, his fingertips brushing her ass. They started kissing, teasingly. Small, almost chaste, noisy kisses that did nothing but make them want to speed up and deepen their contact. It made Dean want to turn on the radio.

Jess must have been able to read his mind because she stopped kissing Sam long enough to say “Don’t you dare,” and then start deepening the kisses. She and Sam rocked into each other, shallow and light and just enough to make their breathing deeper.  It sounded loud in the confined space of the impala. It got impossibly louder when Sam grabbed onto Jess’ ass and pulled her down against him where he was thickening in his jeans and he bucked up.

“Dean, get off the highway and onto a backstreet,” Sam commanded in between kisses and cut off grunts. “I want to get these perfect tits out.”

Sam punctuated that by running his hands up to Jess’ breasts and squeezing, thumbs brushing over her nipples, knowing exactly where they were under her clothing. Jess let out a sigh of pleasure.

“You ever notice how perfect they are, Dean? How Jess likes it whenever you just tease at her nipples? How perfect it feels to get those pretty pink nipples hard in your mouth?”

“Fuck, Sam,” Dean breathed from the driver’s seat. Sam and Jess smirked into each other’s mouths.

Jess lifted her head so Sam could suck kisses down her neck. “You’d better get on a back road so I can turn around and you can watch Sam play with my nipples while he presses that hard cock against me. Maybe I’ll even let him fuck me back here while you have to keep driving and watch through the rearview.”

Dean whined but he was off the highway and onto some country road that took them the same direction in a heartbeat. He honestly had no idea how fast he’d gotten the car to move with just the sounds of Jess and Sam grinding on each other and making out in the back seat. When he glanced in the rearview, Jess was turned around, ass to Sam’s lap, and Sam had her shirt off and his hands were cupping her breasts through her bra. Dean could tell her was pinching and rolling and her nipples and Jess’ head was thrown back onto Sam’s shoulder. He was biting at her neck. Dean desperately wanted to pull over and take his hard dick into his own hand if they weren’t going to offer to let him join them in the backseat, but he hadn’t been given permission.

Dean heard Sam undo Jess’ zipper, even over the sound of the impala trekking over gravel and her engine. He could faintly hear the wet sounds of Sam bringing a hand down to Jess’ sex, sliding his fingers into her panties. When he glanced in the rearview again, he could see he was right. Jess had her eyes closed in pleasure and was writhing in a slow rhythm and her mouth was parted. Dean didn’t even know he was making noise until Sam laughed into Jess’ skin.

“Something wrong, Dean?” Jess opened her eyes when Sam asked and she could see that Dean was shifting around in his seat.

“I don’t think anything’s wrong for him, Sam,” she said. Dean glanced into the rearview again and Jess caught his eye. She smirked and gasped when Sam bit her neck again and his one hand pressed hard against her sex. She went on either way. “I think he likes being teased. I think he wants to listen to you fuck me back here.”

“Please, no. I’ll crash the car,” Dean told them, his voice on the verge of begging.

“Then pull over,” Sam said. He’d moved to nibbling on Jess’ ear lobe as he rubbed circles around her clit with his hand down her panties. Jess groaned. “Because I’m going to fuck this tight little ass back here and then you’re going to wait until we tell you what to do.”

Jess and Dean both moaned and Dean pulled the car over immediately.

“You’re so obedient, Dean,” Sam teased.

“Oh fuck you, just hurry up so I can touch myself,” Dean snapped.  He grimaced as soon as the words were out of his mouth.

“See, now I’m just going to take my time. Make sure I get my fingers nice and wet from her pussy before I open up her ass. Spread this slick all over her hole so I can slide in real slow,” Sam said. He was teasing at Jess’ cunt while he said it and she was shimmying out of her pants completely. Sam stopped long enough to let her get her panties off too. He made no move to even unzip his pants yet.

“Make sure you keep your hands on the steering wheel, Dean,” Jess said between breaths. “I have plans for you and they don’t involve you coming soon.”

Dean’s knuckles were white as he gripped the steering wheel in a perfect 10 and 2 position he never used and tried not to squirm in his seat to get friction against his cock. He briefly wondered if this would be the day that Sam and Jess’ combined dirty mouths would get him off without a single touch and he’d be stuck sitting in his car having creamed his jeans while his baby brother fucked a girl in the ass. The thought made his dick twitch. There was a wet spot forming in his boxers.

Jess kept rubbing herself against Sam’s hand as he spread her wetness around. His palm ground against her clit and Jess couldn’t help but speed up and chase her release.

“Go ahead, Jess. Get off so I can use your come to slick you up. I want you to feel good,” Sam said in her ear, loud enough Dean could hear but soft enough that it was still a whisper of sorts. Sam moved his fingers again so he was just shallowly dipping into Jess and rubbing his palm against her and his breath was hot on her neck and ear. He just kept kissing her and nibbling at her and he let her set the pace until she was nearly to her climax. Then he fucked his fingers up into her and put more pressure on her clit as he brought his other hand down and she was coming and bucking into him. She keened low and long as her muscles clenched around Sam’s fingers in orgasm.

She hadn’t even come down yet when he was pulling out and wiping her come against her ass hole, finger tips teasing at it. He pushed two in up to the first knuckle to get her wet. Jess felt like she was a mess of her own fluids and she could feel Sam’s bare cock‒ when he’d gotten his pants undone, she didn’t know. She was so lost in the feeling of Sam and riding the last of her orgasm that she didn’t even notice Dean’s quiet curses from the front seat. She felt pliant and amazing.

Sam’s fingers were deep inside her before she knew it and she felt full and good and she wanted him to fuck her. His other hand still was teasing at her clit as she fucked in and out of her ass shallowly.

“Get your dick in me, please,” she told Sam, reaching an arm back and fisting into his hair.  He didn’t bother to reply verbally, just maneuvered himself so his cock was pressed against her.

“Fuck yourself onto me, then,” he said. Jess wasted no time and pushed herself back, hissing at the stretch of Sam’s cock when she didn’t have enough lubrication but loving it nonetheless. There was a reason she let him take charge, after all. They both groaned when he bottomed out in her. His one hand circled her clit and played at the entrance of her cunt alternatively.

Dean was practically dying in the front seat. He somehow managed to keep his hands on the steering wheel but he couldn’t stop his hips from moving back and forth, getting his pants to rub against his hard-on.  His zipper pushed against him and hurt but he couldn’t get enough of it because it was friction and he needed it. He could barely look at Jess and Sam at the same time he couldn’t look away from them.   

He felt as though time had stretched out impossibly as he watched Sam bounce Jess on his lap, his cock filling her ass. Jess gave out breathy moans with every thrust and Sam had barely stopped playing with her clit since her first orgasm and he didn’t seem to want to stop any time soon. The smell of sex and sweat filled the impala and Dean thought his mouth might be watering.

Jess had her hands on her nipples, teasing and pulling and her lip got caught between her teeth every few thrusts.

She moaned. “Fuck, Sam.”

“Do you want me to come in you? You want me to fill you up?” Sam thrust up and pressed against Jess’ clit and rubbed and Dean couldn’t tear his eyes away as Jess squeezed her breasts and came again.

The veins in Sam’s neck stood out as he came with Jess’ ass tightening around him, milking his orgasm from him. His hands clutched at her hips and kept her pulled close to his lap, kept her split on him.

They were barely coming down when they heard Dean begging.

“Please, please let me touch myself, let me come.”

Sam kissed the back of Jess neck, licking at the sweat there, and then leaned forward. “Go up to the front seat. Don’t bother getting dressed.”

Jess couldn’t stop herself from looking around to make sure there were no cars before she ran out to get in the front seat. The snacks were flung to the foot well. She pressed up to Dean as soon as she was in the front seat and tried not to think about the mess dripping down between her legs. She hadn’t bothered to close the door and she only heard it slam a moment later when he tongue was already in Dean’s mouth. She was half way onto his lap when she felt Sam’s hand wrap around her calf and he heard the door slam behind her.

Sam pulled Jess away from Dean and both of them whined. Sam situated Jess so she was bent over his lap with her ass in the air. He brought a hand to her ass and palmed at her cheek, letting two fingers slide into her crack and play with the slickness there.

“Get back on the road, Dean,” Sam ordered. Dean shot a horrified look over at Sam over Jess. She had her head on his thigh and her breath was hot through his jeans. It ghosted across his fly and he wanted to scream. He stared at Sam and Jess inhaled sharply. Sam looked back at him and sunk a fingertip into Jess’ ass as he repeated himself. “Get back on the road.”

Dean felt as though he could barely see straight to follow that order, but he managed to do so. The impala shook on the unfinished gravel road just enough that the vibrations moved through the seat.

Over the pinging of rocks, Dean heard Sam slap Jess’ ass and he could feel her keen.

“Get it up higher so I can eat myself out of you.”

“Holy fuck, Sam,” Dean groaned, his hands jerking on the wheel.

“Keep us steady or I won’t tell Jess to take your dick out of your jeans and suck you off.”

“Please,” Jess said. “Please let me make Dean feel good while you eat my ass, Sam. Let me taste Dean while you taste yourself, baby, please?”

Jess so rarely had to ask for anything in bed that it was the prettiest sound to Sam’s ears. He leaned down and gave a teasing bite to one of Jess’ cheeks. He spread her apart and moved and brought his tongue to her slit, dragging from her pussy to her ass. He swirled his tongue around, lapping at his own come from her. He paused only long enough to tell her to suck Dean off and for Dean to keep his hands on the wheel and drive and went back to licking Jess.

Jess moaned at the way Sam was opening her up and emptying her on his tongue and set to working on undoing Dean’s pants. He lifted off the seat enough for the two of them to manage to get his jeans and boxers low enough that his cock sprung up, glistening with pre-come at the tip. Jess wrapped a hand around him and her thumb spread the slick around his crown.

“Fuck, please, Jess, please don’t tease.” Her eyes tilted up and she started to smirk at him but then her eyes rolled up and closed. Sam’d brought a hand to her pussy and pushed two fingers in. He angled so he could thumb at her still over sensitive clit back and forth. She wanted to feel as full as she could. She lowered her mouth and swallowed Dean down as far as she could, her nose hitting his thigh.

Dean groaned so loud it was nearly a scream and his hips bucked up on their own. Jess held back a gag but spit was pooling in her mouth. She let it slide from her lips and down to Dean’s balls. She started to bob her head to the same speed Sam was thrusting his tongue into the pucker of her ass. Even though her legs felt weak from the way she’d been climbing around and the orgasms she’d already had, she felt amazing and she wanted Dean to feel as good as she and Sam had earlier. She twisted her neck on every bob up she could and she could hear a small stutter of breath from Dean with every movement.

Sam thrust his fingers into her deeper and crooked up and pressed his thumb against her clit and closed his lips around her hole and sucked and she was coming for a third time. Her mouth went slack around Dean but his hips were snapping up and his cock hit her throat with each one and  when Jess regained control of herself she closed her mouth around the head of Dean’s dick and sucked. He took his foot off the gas pedal and a hand off the wheel to wrap in her hair as he came hard down Jess’ throat with a cry.

The impala had come to a stop by the time Jess straightened up and moved so that she was sitting between Sam and Dean. She was naked and wet and she knew she was leaving a mark on the seat and she could smell her sex, but she just started to laugh.

Dean was breathing too hard to join her and Sam digging in the glove compartment. He found what he was looking for in a package baby wipes and passed one to Jess.

“Was that your plan all along, Sam?” Jess asked while she cleaned herself off.  “Did you wake up this morning and think ‘road head’ seems like a good idea?”

Sam shrugged with a grin. Jess laughed at him again.

“Well whatever put it in your head can come back,” Dean said with a leer having recovered.  Jess rolled her eyes but Sam’s grin turned into a smirk.

“Oh, whatever it was will show up again. But probably when I’m gonna drive next time.” 


End file.
